Methyl 3-(cyclopentylamino)propanoate synthesis
- Product Name:Methyl 3-(cyclopentylamino)propanoate
- CAS Number:754125-43-4
- Molecular formula:C9H17NO2
- Molecular Weight:171.2368
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Yield: 55%
Reaction Conditions:
Stage #1:methyl 3-aminopropanoate;cyclopentanone with sodium acetate;sodium tris(acetoxy)borohydride in dichloromethane at 20; for 16 h;
Stage #2: with sodium hydroxide;water;sodium hydrogencarbonate in dichloromethaneProduct distribution / selectivity;
Steps:
1.2; 2.1.2
Step 2: Methyl 3-(cyclopentylamino)propanoate; Methyl 3-aminopropanoate (9.37 g, 0.09 mol) was solubilised in DCM (200 ml) and cyclopentanone (6.43 ml, 0.07 mol), sodium acetate (5.96 g, 0.07 mol) and sodium triacetoxyborohydride (22 g, 0.10 mol) were added. The reaction was stirred at rt for 16h. 20% sodium bicarbonate (100 ml) and 2M sodium hydroxide (50 ml) were then added and the product extracted using DCM/η2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give the product as a pale yellow oil (8.90 g, 55%); MS+ve: 172.4.
References:
CYCLACEL LIMITED WO2009/40556, 2009, A1 Location in patent:Page/Page column 44; 75
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754125-43-4
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754125-43-4
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